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Trimethylphosphine → (E)-ethyl 3-(4-(4-(N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)sulfamoyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate

HRID 870183
Notes
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Reaction equation

HRID 870183 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:41]=[CH:40][C:22]([O:23][C:24]2[C:29]([F:30])=[CH:28][C:27](/[CH:31]=[C:32](\[CH3:38])/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:26][C:25]=2[F:39])=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[N+]=[N-].CP(C)C>C1COCC1.O>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:41]=[CH:40][C:22]([O:23][C:24]2[C:25]([F:39])=[CH:26][C:27](/[CH:31]=[C:32](\[CH3:38])/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:28][C:29]=2[F:30])=[CH:21][CH:20]=1)(=[O:18])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 86672339(E)-ethyl 3-(4-(4-(N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)sulfamoyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate

Product 1

HCID 70906018(E)-ethyl 3-(4-(4-(N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)sulfamoyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylateYield 101%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of (E)-ethyl 3-(4-(4-(N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)sulfamoyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate (169 mg, 0.28 mmol) in THF (6 ml) and water (0.6 mL) under nitrogen was added trimethylphosphine (26 mg, 0.34 mmol). After stirring for 3 hours, the solvents were removed at reduced pressure and. The residue was dissolved in water (5 mL) and extracted with EtOAc (3×25 mL). The combined organic layers were dried (Na2SO4) and concentrated to give the title compound (162 mg).

Workup

  1. customthe solvents were removed at reduced pressure
  2. dissolutionThe residue was dissolved in water (5 mL)
  3. extractionextracted with EtOAc (3×25 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c8e97d8e0af449d2a5ca520f8bd74e27
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969377B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes